NPASS Compound

Structure

NPC475192 OpenBabel07101719122D 21 21 0 0 1 0 0 0 0 0999 V2000 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 11 2 0 0 0 0 4 11 1 0 0 0 0 5 6 1 0 0 0 0 5 10 2 0 0 0 0 6 12 1 0 0 0 0 7 12 1 0 0 0 0 7 14 2 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 13 1 0 0 0 0 9 15 1 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 17 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.15
Volume:	313.374
LogP:	3.675
LogD:	1.583
LogS:	-3.69
# Rotatable Bonds:	6
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.704
Synthetic Accessibility Score:	3.254
Fsp3:	0.353
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.048
MDCK Permeability:	7.575257313874317e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.104
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.944
30% Bioavailability (F30%):	0.413

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	86.9526138305664%
Volume Distribution (VD):	0.476
Pgp-substrate:	9.651128768920898%

ADMET: Metabolism

CYP1A2-inhibitor:	0.109
CYP1A2-substrate:	0.113
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.078

ADMET: Excretion

Clearance (CL):	7.511
Half-life (T1/2):	0.934

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.79
Drug-inuced Liver Injury (DILI):	0.898
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.094
Maximum Recommended Daily Dose:	0.169
Skin Sensitization:	0.165
Carcinogencity:	0.045
Eye Corrosion:	0.004
Eye Irritation:	0.126
Respiratory Toxicity:	0.082

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC475192

Natural Product ID:	NPC475192
*Common Name:**	4-Hydroxy-3-(2-Hydroxy-3-Methylbut-3-Enyl)-5-(3-Methylbut-2-Enyl)Benzoic Acid
IUPAC Name:	4-hydroxy-3-(2-hydroxy-3-methylbut-3-enyl)-5-(3-methylbut-2-enyl)benzoic acid
Synonyms:
Standard InCHIKey:	XARKMPGLVZWUBR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H22O4/c1-10(2)5-6-12-7-14(17(20)21)8-13(16(12)19)9-15(18)11(3)4/h5,7-8,15,18-19H,3,6,9H2,1-2,4H3,(H,20,21)
SMILES:	CC(=CCc1cc(cc(c1O)CC(C(=C)C)O)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500668
PubChem CID:	25111594
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO16463	Piper glabratum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18712933]
NPO16463	Piper glabratum	Species	Piperaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18712933]
NPO16463	Piper glabratum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	IC50	=	67.6	ug.mL-1	PMID[568451]
NPT1208	Organism	Leishmania braziliensis	Leishmania braziliensis	IC50	=	67.6	ug.mL-1	PMID[568451]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	67.3	ug.mL-1	PMID[568451]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	>	20.0	ug.mL-1	PMID[568451]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	10.0	ug.mL-1	PMID[568451]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC475192 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	1048
0.2-0.3	2906
0.3-0.4	7292
0.4-0.5	12134
0.5-0.6	5422
0.6-0.7	9680
0.7-0.8	3737
0.8-0.85	197
0.85-0.9	38
0.9-0.95	10
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9391	High Similarity	NPC83718
0.9344	High Similarity	NPC473744
0.9231	High Similarity	NPC474890
0.9231	High Similarity	NPC161943
0.9231	High Similarity	NPC273282
0.9153	High Similarity	NPC473767
0.912	High Similarity	NPC473777
0.9055	High Similarity	NPC204582
0.8871	High Similarity	NPC473751
0.8862	High Similarity	NPC184219
0.8852	High Similarity	NPC67300
0.878	High Similarity	NPC174991
0.8769	High Similarity	NPC475111
0.875	High Similarity	NPC302844
0.874	High Similarity	NPC123
0.874	High Similarity	NPC163169
0.872	High Similarity	NPC110211
0.8682	High Similarity	NPC139074
0.8682	High Similarity	NPC213485
0.8682	High Similarity	NPC40524
0.8667	High Similarity	NPC174087
0.8651	High Similarity	NPC121104
0.8644	High Similarity	NPC242136
0.8583	High Similarity	NPC229894
0.8571	High Similarity	NPC474945
0.8571	High Similarity	NPC474944
0.8571	High Similarity	NPC204579
0.8571	High Similarity	NPC476022
0.8561	High Similarity	NPC477592
0.855	High Similarity	NPC283590
0.855	High Similarity	NPC70859
0.855	High Similarity	NPC61153
0.855	High Similarity	NPC130899
0.8538	High Similarity	NPC239855
0.8527	High Similarity	NPC475042
0.8516	High Similarity	NPC117899
0.8507	High Similarity	NPC469911
0.8468	Intermediate Similarity	NPC295034
0.8444	Intermediate Similarity	NPC184053
0.8438	Intermediate Similarity	NPC193203
0.8438	Intermediate Similarity	NPC476024
0.84	Intermediate Similarity	NPC91105
0.8387	Intermediate Similarity	NPC216216
0.8385	Intermediate Similarity	NPC18798
0.8359	Intermediate Similarity	NPC209959
0.8358	Intermediate Similarity	NPC477593
0.8346	Intermediate Similarity	NPC475733
0.8346	Intermediate Similarity	NPC49938
0.8346	Intermediate Similarity	NPC472592
0.8333	Intermediate Similarity	NPC65761
0.8333	Intermediate Similarity	NPC477594
0.8333	Intermediate Similarity	NPC472029
0.8333	Intermediate Similarity	NPC474394
0.832	Intermediate Similarity	NPC215392
0.832	Intermediate Similarity	NPC303737
0.8305	Intermediate Similarity	NPC95172
0.8293	Intermediate Similarity	NPC94298
0.8293	Intermediate Similarity	NPC249435
0.8293	Intermediate Similarity	NPC27633
0.8291	Intermediate Similarity	NPC29883
0.8279	Intermediate Similarity	NPC131192
0.8276	Intermediate Similarity	NPC243677
0.8271	Intermediate Similarity	NPC477596
0.8268	Intermediate Similarity	NPC474803
0.8268	Intermediate Similarity	NPC117794
0.8264	Intermediate Similarity	NPC114918
0.8264	Intermediate Similarity	NPC197513
0.8258	Intermediate Similarity	NPC180261
0.8258	Intermediate Similarity	NPC37299
0.8254	Intermediate Similarity	NPC297193
0.8254	Intermediate Similarity	NPC309765
0.8244	Intermediate Similarity	NPC471851
0.824	Intermediate Similarity	NPC149246
0.8235	Intermediate Similarity	NPC64664
0.8231	Intermediate Similarity	NPC476119
0.8231	Intermediate Similarity	NPC474998
0.8222	Intermediate Similarity	NPC94248
0.8222	Intermediate Similarity	NPC475974
0.8222	Intermediate Similarity	NPC212693
0.8217	Intermediate Similarity	NPC100067
0.8217	Intermediate Similarity	NPC103356
0.8217	Intermediate Similarity	NPC266689
0.8217	Intermediate Similarity	NPC23126
0.8217	Intermediate Similarity	NPC30501
0.8217	Intermediate Similarity	NPC98254
0.8217	Intermediate Similarity	NPC105157
0.8217	Intermediate Similarity	NPC72158
0.8217	Intermediate Similarity	NPC190043
0.8217	Intermediate Similarity	NPC169250
0.8217	Intermediate Similarity	NPC162612
0.8211	Intermediate Similarity	NPC160199
0.8209	Intermediate Similarity	NPC84699
0.8205	Intermediate Similarity	NPC184658
0.8203	Intermediate Similarity	NPC240744
0.8203	Intermediate Similarity	NPC167055
0.8201	Intermediate Similarity	NPC97188
0.8195	Intermediate Similarity	NPC202225
0.8189	Intermediate Similarity	NPC275145
0.8182	Intermediate Similarity	NPC211421
0.8175	Intermediate Similarity	NPC472604
0.8175	Intermediate Similarity	NPC472605
0.8175	Intermediate Similarity	NPC477595
0.8175	Intermediate Similarity	NPC31936
0.8168	Intermediate Similarity	NPC247477
0.8168	Intermediate Similarity	NPC17840
0.8168	Intermediate Similarity	NPC327457
0.8168	Intermediate Similarity	NPC86774
0.8167	Intermediate Similarity	NPC212718
0.8167	Intermediate Similarity	NPC114682
0.8162	Intermediate Similarity	NPC19622
0.8162	Intermediate Similarity	NPC112789
0.8154	Intermediate Similarity	NPC3009
0.8154	Intermediate Similarity	NPC221777
0.8154	Intermediate Similarity	NPC21305
0.8154	Intermediate Similarity	NPC473017
0.8154	Intermediate Similarity	NPC2596
0.8148	Intermediate Similarity	NPC178467
0.8148	Intermediate Similarity	NPC474849
0.8148	Intermediate Similarity	NPC70380
0.8148	Intermediate Similarity	NPC65837
0.8148	Intermediate Similarity	NPC149372
0.8148	Intermediate Similarity	NPC474771
0.8148	Intermediate Similarity	NPC71256
0.8148	Intermediate Similarity	NPC194579
0.814	Intermediate Similarity	NPC62952
0.814	Intermediate Similarity	NPC267846
0.8136	Intermediate Similarity	NPC226699
0.8134	Intermediate Similarity	NPC470210
0.8134	Intermediate Similarity	NPC290803
0.8134	Intermediate Similarity	NPC278375
0.812	Intermediate Similarity	NPC303141
0.812	Intermediate Similarity	NPC78307
0.8116	Intermediate Similarity	NPC321980
0.8116	Intermediate Similarity	NPC470087
0.8115	Intermediate Similarity	NPC474050
0.8115	Intermediate Similarity	NPC474114
0.8115	Intermediate Similarity	NPC473931
0.811	Intermediate Similarity	NPC68167
0.811	Intermediate Similarity	NPC282577
0.8106	Intermediate Similarity	NPC198249
0.8106	Intermediate Similarity	NPC275504
0.8102	Intermediate Similarity	NPC275903
0.8102	Intermediate Similarity	NPC472600
0.8102	Intermediate Similarity	NPC472601
0.8102	Intermediate Similarity	NPC471853
0.8095	Intermediate Similarity	NPC146642
0.8095	Intermediate Similarity	NPC165197
0.8092	Intermediate Similarity	NPC474546
0.8092	Intermediate Similarity	NPC102829
0.8092	Intermediate Similarity	NPC120488
0.8092	Intermediate Similarity	NPC194979
0.8088	Intermediate Similarity	NPC9121
0.8088	Intermediate Similarity	NPC177307
0.8088	Intermediate Similarity	NPC191835
0.8088	Intermediate Similarity	NPC221104
0.8088	Intermediate Similarity	NPC112135
0.8088	Intermediate Similarity	NPC472403
0.808	Intermediate Similarity	NPC476020
0.808	Intermediate Similarity	NPC182240
0.8077	Intermediate Similarity	NPC116513
0.8074	Intermediate Similarity	NPC118919
0.8074	Intermediate Similarity	NPC291454
0.8067	Intermediate Similarity	NPC470039
0.8062	Intermediate Similarity	NPC201728
0.8062	Intermediate Similarity	NPC262671
0.8058	Intermediate Similarity	NPC148545
0.8058	Intermediate Similarity	NPC471731
0.8058	Intermediate Similarity	NPC294432
0.8058	Intermediate Similarity	NPC51106
0.8058	Intermediate Similarity	NPC159721
0.8051	Intermediate Similarity	NPC6984
0.8049	Intermediate Similarity	NPC322197
0.8047	Intermediate Similarity	NPC477153
0.8045	Intermediate Similarity	NPC110609
0.8045	Intermediate Similarity	NPC242358
0.8045	Intermediate Similarity	NPC246693
0.8043	Intermediate Similarity	NPC470842
0.8043	Intermediate Similarity	NPC472603
0.8033	Intermediate Similarity	NPC28784
0.8033	Intermediate Similarity	NPC296144
0.8033	Intermediate Similarity	NPC11824
0.8031	Intermediate Similarity	NPC25168
0.8031	Intermediate Similarity	NPC226275
0.803	Intermediate Similarity	NPC109778
0.803	Intermediate Similarity	NPC470987
0.803	Intermediate Similarity	NPC21378
0.803	Intermediate Similarity	NPC282230
0.803	Intermediate Similarity	NPC183348
0.803	Intermediate Similarity	NPC245395
0.8029	Intermediate Similarity	NPC105456
0.8029	Intermediate Similarity	NPC139634
0.8029	Intermediate Similarity	NPC474655
0.8028	Intermediate Similarity	NPC17600
0.8017	Intermediate Similarity	NPC228609
0.8016	Intermediate Similarity	NPC473136
0.8016	Intermediate Similarity	NPC294037
0.8016	Intermediate Similarity	NPC159525
0.8015	Intermediate Similarity	NPC470981
0.8015	Intermediate Similarity	NPC475957
0.8014	Intermediate Similarity	NPC473023

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC475192 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	790
0.2-0.3	1598
0.3-0.4	2591
0.4-0.5	2186
0.5-0.6	1161
0.6-0.7	515
0.7-0.8	81
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8374	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD9545	Approved
0.8291	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD2935	Discontinued
0.7786	Intermediate Similarity	NPD4628	Phase 3
0.7786	Intermediate Similarity	NPD1164	Approved
0.7754	Intermediate Similarity	NPD5408	Approved
0.7754	Intermediate Similarity	NPD5406	Approved
0.7754	Intermediate Similarity	NPD5404	Approved
0.7754	Intermediate Similarity	NPD5405	Approved
0.7721	Intermediate Similarity	NPD230	Phase 1
0.7698	Intermediate Similarity	NPD9493	Approved
0.7692	Intermediate Similarity	NPD2533	Approved
0.7692	Intermediate Similarity	NPD2534	Approved
0.7692	Intermediate Similarity	NPD2532	Approved
0.7692	Intermediate Similarity	NPD9269	Phase 2
0.7656	Intermediate Similarity	NPD9268	Approved
0.7623	Intermediate Similarity	NPD74	Approved
0.7623	Intermediate Similarity	NPD9266	Approved
0.7623	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4380	Phase 2
0.7541	Intermediate Similarity	NPD9267	Approved
0.7541	Intermediate Similarity	NPD9264	Approved
0.7541	Intermediate Similarity	NPD9263	Approved
0.75	Intermediate Similarity	NPD3764	Approved
0.7483	Intermediate Similarity	NPD7075	Discontinued
0.7448	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2799	Discontinued
0.7429	Intermediate Similarity	NPD1510	Phase 2
0.7413	Intermediate Similarity	NPD3400	Discontinued
0.74	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1240	Approved
0.7391	Intermediate Similarity	NPD943	Approved
0.7388	Intermediate Similarity	NPD1470	Approved
0.7383	Intermediate Similarity	NPD7411	Suspended
0.7379	Intermediate Similarity	NPD7390	Discontinued
0.7372	Intermediate Similarity	NPD2313	Discontinued
0.7365	Intermediate Similarity	NPD7458	Discontinued
0.7348	Intermediate Similarity	NPD1201	Approved
0.7333	Intermediate Similarity	NPD6801	Discontinued
0.7329	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD6004	Phase 3
0.7324	Intermediate Similarity	NPD6002	Phase 3
0.7324	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD6005	Phase 3
0.7303	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD1237	Approved
0.7292	Intermediate Similarity	NPD7003	Approved
0.7292	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD1809	Phase 2
0.7286	Intermediate Similarity	NPD1607	Approved
0.7285	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD7819	Suspended
0.7273	Intermediate Similarity	NPD1549	Phase 2
0.7266	Intermediate Similarity	NPD5951	Approved
0.7266	Intermediate Similarity	NPD9281	Approved
0.7246	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6190	Approved
0.7213	Intermediate Similarity	NPD1930	Approved
0.7213	Intermediate Similarity	NPD9261	Approved
0.7213	Intermediate Similarity	NPD1929	Approved
0.7213	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4626	Approved
0.719	Intermediate Similarity	NPD7768	Phase 2
0.7188	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3750	Approved
0.717	Intermediate Similarity	NPD5844	Phase 1
0.7167	Intermediate Similarity	NPD9495	Approved
0.7165	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD9717	Approved
0.7163	Intermediate Similarity	NPD6651	Approved
0.7155	Intermediate Similarity	NPD9256	Approved
0.7155	Intermediate Similarity	NPD9258	Approved
0.7154	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6799	Approved
0.7143	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2796	Approved
0.7132	Intermediate Similarity	NPD2629	Approved
0.7131	Intermediate Similarity	NPD846	Approved
0.7131	Intermediate Similarity	NPD940	Approved
0.7124	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD845	Approved
0.7103	Intermediate Similarity	NPD2800	Approved
0.7097	Intermediate Similarity	NPD5048	Discontinued
0.7089	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2346	Discontinued
0.7077	Intermediate Similarity	NPD256	Approved
0.7077	Intermediate Similarity	NPD255	Approved
0.7071	Intermediate Similarity	NPD6663	Approved
0.707	Intermediate Similarity	NPD6232	Discontinued
0.7063	Intermediate Similarity	NPD7033	Discontinued
0.7063	Intermediate Similarity	NPD2182	Approved
0.7037	Intermediate Similarity	NPD3972	Approved
0.7029	Intermediate Similarity	NPD9494	Approved
0.7029	Intermediate Similarity	NPD5736	Approved
0.7029	Intermediate Similarity	NPD4208	Discontinued
0.702	Intermediate Similarity	NPD3226	Approved
0.702	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD1551	Phase 2
0.7007	Intermediate Similarity	NPD1203	Approved
0.7	Intermediate Similarity	NPD2860	Approved
0.7	Intermediate Similarity	NPD6798	Discontinued
0.7	Intermediate Similarity	NPD2859	Approved
0.7	Intermediate Similarity	NPD920	Approved
0.6993	Remote Similarity	NPD1934	Approved
0.6992	Remote Similarity	NPD5691	Approved
0.6986	Remote Similarity	NPD1243	Approved
0.6978	Remote Similarity	NPD6832	Phase 2
0.6974	Remote Similarity	NPD6599	Discontinued
0.6972	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6355	Discontinued
0.6972	Remote Similarity	NPD5124	Phase 1
0.6967	Remote Similarity	NPD3020	Approved
0.6966	Remote Similarity	NPD2344	Approved
0.6962	Remote Similarity	NPD5710	Approved
0.6962	Remote Similarity	NPD5711	Approved
0.6957	Remote Similarity	NPD2798	Approved
0.6957	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.695	Remote Similarity	NPD520	Approved
0.6944	Remote Similarity	NPD4308	Phase 3
0.694	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.694	Remote Similarity	NPD2932	Approved
0.694	Remote Similarity	NPD3019	Approved
0.6939	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD8166	Discontinued
0.6937	Remote Similarity	NPD7473	Discontinued
0.6935	Remote Similarity	NPD6647	Phase 2
0.6934	Remote Similarity	NPD1283	Approved
0.6933	Remote Similarity	NPD6273	Approved
0.6929	Remote Similarity	NPD7008	Discontinued
0.6929	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD2934	Approved
0.6917	Remote Similarity	NPD1759	Phase 1
0.6917	Remote Similarity	NPD2933	Approved
0.6917	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD1608	Approved
0.6899	Remote Similarity	NPD6959	Discontinued
0.6897	Remote Similarity	NPD4476	Approved
0.6897	Remote Similarity	NPD4477	Approved
0.6889	Remote Similarity	NPD3496	Discontinued
0.6884	Remote Similarity	NPD2797	Approved
0.688	Remote Similarity	NPD164	Approved
0.6879	Remote Similarity	NPD3268	Approved
0.6871	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD5953	Discontinued
0.6867	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.686	Remote Similarity	NPD844	Approved
0.6857	Remote Similarity	NPD4207	Discontinued
0.6853	Remote Similarity	NPD447	Suspended
0.6852	Remote Similarity	NPD7286	Phase 2
0.6849	Remote Similarity	NPD7266	Discontinued
0.6846	Remote Similarity	NPD7236	Approved
0.6846	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1758	Phase 1
0.6835	Remote Similarity	NPD1019	Discontinued
0.6833	Remote Similarity	NPD1202	Approved
0.6829	Remote Similarity	NPD2066	Phase 3
0.6829	Remote Similarity	NPD6559	Discontinued
0.6828	Remote Similarity	NPD3748	Approved
0.6821	Remote Similarity	NPD5049	Phase 3
0.6815	Remote Similarity	NPD1778	Approved
0.681	Remote Similarity	NPD9259	Approved
0.681	Remote Similarity	NPD9257	Approved
0.6797	Remote Similarity	NPD3455	Phase 2
0.6795	Remote Similarity	NPD3817	Phase 2
0.6794	Remote Similarity	NPD1241	Discontinued
0.6791	Remote Similarity	NPD1894	Discontinued
0.679	Remote Similarity	NPD3818	Discontinued
0.6788	Remote Similarity	NPD1481	Phase 2
0.6783	Remote Similarity	NPD825	Approved
0.6783	Remote Similarity	NPD2979	Phase 3
0.6783	Remote Similarity	NPD826	Approved
0.6783	Remote Similarity	NPD4060	Phase 1
0.6781	Remote Similarity	NPD9570	Approved
0.6779	Remote Similarity	NPD3887	Approved
0.6779	Remote Similarity	NPD2309	Approved
0.6776	Remote Similarity	NPD5403	Approved
0.6774	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD3134	Approved
0.677	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6166	Phase 2
0.6767	Remote Similarity	NPD9568	Approved
0.6765	Remote Similarity	NPD3847	Discontinued
0.6761	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD411	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data